Shelter Island Vacations

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Where to stay in Shelter Island

Find the best Shelter Island areas and neighborhoods for the activities you enjoy most. Learn more about Shelter Island

Find the Best Shelter Island Vacation Packages

Shelter Island Beach Vacation

There's nothing like a Shelter Island vacation to give you a little extra bounce in your step. The sound of rolling surf and the smell of clean ocean air are sure to refresh your mind, body and soul. To be close to the town center on your trip to Shelter Island, find a hotel around Wades Beach (2 kilometers away). If you're planning to stay for a bit, look into our Shelter Island packages. Not only can you save some cash, you'll also have other amazing beaches near you to explore, like Shell Beach and Menhadden Lane Beach.

Shelter Island Hotel Deals

Gurney's Montauk Resort & Seawater Spa

Gurney's Montauk Resort & Seawater Spa

4 out of 5
290 Old Montauk Highway Montauk NY
The price is ₩569,218 per night from Mar 26 to Mar 27
₩569,218
₩780,397 total
Mar 26 - Mar 27
includes taxes & fees
8.4/10 Very Good! (744 reviews)
Staff was friendly. Language smetimes a problem. Room was perfect. Property had easy access for disabled person w/ cane.

Reviewed on Mar 24, 2026

Gurney's Montauk Resort & Seawater Spa
Montauk Manor

Montauk Manor

3.5 out of 5
236 Edgemere St. Montauk NY
The price is ₩225,008 per night from Mar 26 to Mar 27
₩225,008
₩286,231 total
Mar 26 - Mar 27
includes taxes & fees
9.2/10 Wonderful! (1,307 reviews)
Everything was lovely. It was a wonderful place to relax after a long day of sightseeing.

Reviewed on Mar 23, 2026

Montauk Manor
Water's Edge Resort & Spa

Water's Edge Resort & Spa

3.5 out of 5
1525 Boston Post Road Westbrook CT
Fully refundableReserve now, pay when you stay
The price is ₩316,130 per night from Mar 29 to Mar 30
₩316,130
₩389,220 total
Mar 29 - Mar 30
includes taxes & fees
8.8/10 Excellent! (1,007 reviews)
The room was perfect, staff was excellent, parking was right next to my room. Best Breakfast Sausage ever.

Reviewed on Mar 24, 2026

Water's Edge Resort & Spa
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.